Oil/fat composition

ABSTRACT

An oil/fat composition comprising 5 to 99.9 wt. % of a monoglyccride having, as fatty acid constituents thereof, 15 to 90 wt % of an ω 3-unsaturated fatty acid having less than 20 carbon atoms, 1 to 80 wt. % of an ω 9-unsaturated fatty acid and 2 to 50 wt. % of an ω 9-unsaturated fatty acid; and 0.1 to 49.9 wt. % of a diglyceride, wherein a weight ratio of the diglyceride to the monoglyceride is less than 1 and the content of a polyunsaturated fatty acid having at least 4 carbon-to-carbon double bonds is 20% or less in all the fatty acid constituents. The oil/fat composition according to the present invention has excellent processing properties, good taste and excellent lowering action against glutamic oxaloacetic transaminase (GOT) and glutamic pyruvic transaminase (GPT) levels in blood. It is useful not only for pharmaceuticals but also for preventive or remedial foods of feeds effective for hepatic function disturbances or obesity.

TECHNICAL FIELD

[0001] The present invention relates to an oil/fat composition having aspecific glyceride composition, a specific fatty acid composition,excellent processing properties, and characterized by the ability tolower glutamic oxaloacetic transaminase (GOT) and/or glutamic pyruvictransaminase (GPT) levels in blood. The present composition is alsocharacterized by good body-fat burning activity.

BACKGROUND ART

[0002] Oil or fat lipids possess high caloric contents (9 kcal/g) andthereby food intake containing high quantities of these lipids canpromote obesity and other life-style related diseases.

[0003] Research so far has been mainly directed to the study of fattyacids constituting a triglyceride, a principal component of a lipid.Nutritionally essential fatty acids are, for example, linoleic acid,arachidonic acid and linolenic acid. These fatty acids are known to beutilized in the body as a constituent of a biomembrane or a raw materialof eicosanoids (prostaglandin, thromboxanes, leukotrienes, etc.). Inaddition, it is reported that there is a high possibility that a diethigh in saturated fatty acids can lead to increases in the blood-serumcholesterol level, leading to atherosclerosis or heart disease (Lancet,2, 959(1950)); and that high levels of linoleic acid oil in the dietincreases tumor incidence and size in experimental animals (J. NationalCancer Institute, 66, 517(1971)). It is reported that an oleic-acid-richand saturated-fatty-acid poor diet will lower LDL-cholesterol levels,while maintaining HDL-cholesterol levels, thereby reducing the risk ofheart diseases (J. Lipid Res., 26, 194(1985), New England J. Medicine,314, 745(1988)). In addition, the physiological activity of various ω3-unsaturated fatty acids, including antithrombus effects ofeicosapentaenoic acid, contained in fish oil has drawn attention (Ann.Rev. Nutr., 8, 517(1988)). However, owing to the high degree ofunsaturation of eicosapentaenoic acid and docosahexaenoic acid, thesecompounds have reduced stability to oxidation; and eicosapentaenoic acidis a known anticoagulant. Based on a study of the intake balance ofthese fatty acids, research reports recommend a ratio of saturated fattyacids: mono-unsaturated fatty acid polyunsaturated fatty acid or a ratioof ω 6-unsaturated fatty acid: ω 3-unsaturated fatty acid. Research inthis area is still in progress (“Nutrition and Diseases of Oils andFats”, published by Saiwai Shobo, “The 6th edition of RecommendedDietary Allowances for Japanese, Ministry of Health and Welfare”).

[0004] With a view to preventing obesity, substitutes for fats and oilsor non-absorptive fats and oils have been developed and typical onesinclude sucrose fatty acid polyester (U.S. Pat. No. 3,600,186) which canbe excreted without being absorbed into the body so that the caloriesderived from such a fat is essentially 0 kcal/g. There is, however, thepotential problem that these fats can result in anal leakage and alsomay inhibit absorption of fat-soluble vitamins. Moreover, these fats donot have food value as an essential fatty acid. Nevertheless, the use ofthese fats have been authorized by the FDA in 1996, with the restrictionthat semi-solid or solid sucrose fatty acid polyesters, having a meltingpoint of 37.8 to 71.1° C. and containing predetermined amounts ofvitamins A, D, E and K, may be used only for salty snack foods.

[0005] It is also known that medium-chain fatty acid triglycerides (MCT)are not accumulated in the body, but possess poor heat stability.Similar effects have been disclosed for conjugated linoleic acid, fishoil or perilla oil (Lipids, 32, 853(1997), J. Agric. Food Chem., 46,1225(1998)).

[0006] One recent study reported an agent containing a glyceridestructure for lowering the triglyceride concentration in serum (JapanesePatent Application Laid-Open No. 5-310567), but this study focused onlyon the structure of monoglycerides and did not report effects ofmonoglycerides at maximum concentrations.

[0007] The use of polyunsaturated-fatty-acid-containing oil/fat powders(Japanese Patent Application Laid-Open No. 6-172782),polyunsaturated-fatty-acid-containing oil/fat compositions andpolyunsaturated-fatty-acid-containing aqueous foods (Japanese PatentApplication Laid-Open No. 7-39302), have been disclosed wherein theirdispersibility in water is improved by adoption of a polyunsaturatedfatty acid having a monoglyceride structure. These reports, however,only refer generally to physiological effects. Onefish-oil-monoglyceride used in the above-described composition has avery unfavorable taste, is apt to become solid on storage, has a roughmouth feel, must be dissolved by heat for use and is low in linoleicacid, one of the essential fatty acids.

[0008] Accordingly, the object of the present invention is to provide anextremely useful oil/fat composition which has excellent processingproperties, is safe, pleasant tasting, has hepatic function improvingaction, body-fat burning action, and is healthy.

DISCLOSURE OF THE INVENTION

[0009] It has now been found that an oil/fat composition using, incombination, a monoglyceride having specified fatty acid constituentsand a diglyceride has excellent processing properties, is capable oflowering GOT and/or GPT levels in the blood, and has a favorablebody-fat burning activity.

[0010] According to the present invention, an oil/fat compositioncomprising 5 to 99.9 wt. % of a monoglyceride having, as fatty acidconstituents thereof, 15 to 90% of an ω 3-unsaturated fatty acid havingless than 20 carbon atoms, 1 to 80% of an ω 9-unsaturated fatty acid,and 2 to 50% of an ω 6-unsaturated fatty acid, and 0.1 to 49.9% of adiglyceride, wherein a weight ratio of the diglyceride to themonoglyceride is less than 1 and the content of a polyunsaturated fattyacid having at least 4 carbon-to-carbon double bonds is 20% or less ofall the fatty acid constituents. All %'s are given here as weight %'s.Throughout this specification, where ranges are provided for thecomponents all values and sub-ranges between stated numbers are alsoincluded.

DETAILED DESCRIPTION OF THE INVENTION

[0011] The monoglyceride used in the present invention is required tohave, as a fatty acid constituent, 15 to 90%, preferably 20 to 80%, morepreferably 30 to 70%, especially preferably 40 to 65% of an ω3-unsaturated fatty acid having less than 20 carbon atoms. The term “ω3-unsaturated fatty acid” as used herein means an unsaturated fatty acidhaving a first unsaturated bond at the third carbon atom from theω-position and having at least two carbon-to-carbon unsaturated bonds.Specific examples include α-linolenic acid (C18:3, allcis-9,12,15-octadecatrienoic acid) and stearidonic acid (C18:4, allcis-6,9,12,15-octadecatetraenoic acid), with α-linolenic acid beingparticularly preferred.

[0012] The monoglyceride further has, as a fatty acid constituent, 1 to80%, preferably 5 to 60%, more preferably 10 to 50%, especiallypreferably 12 to 30% of an ω 9-unsaturated fatty acid. The ω9-unsaturated fatty acid is a C₈₋₂₄ one, preferably a C₁₆₋₂₂ one.Specific examples include oleic acid, eicosamonoenoic acid anddocosamonoenoic acid, with oleic acid being particularly preferred.

[0013] From the viewpoint of intake balance of fatty acids andphysiologically active effects of the ω 3-unsaturated fatted acid, themonoglyceride is preferred to have, as a remaining fatty acidconstituent, 2 to 50%, preferably 5 to 40%, more preferably 10 to 30% ofan ω 6-unsaturated fatty acid having 18 to 22 carbon atoms such aslinoleic acid and γ-linolenic acid. Of these, linoleic acid isparticularly preferred. Unsaturated fatty acids are preferably containedin an amount of 70 to 100%, preferably 80 to 100%, especially 90 to100%. Moreover, from the viewpoint of stability against oxidation andphysiologically active effects, a weight ratio of the content of a fattyacid having at least two carbon-carbon double bonds to the content of (ω9-unsaturated fatty acid+saturated fatty acid) falls within a range offrom 0.7 to 7.5, preferably from 1 to 6, more preferably from 1.2 to 5,especially from 1.5 to 4.

[0014] The oil/fat composition of the present invention contains themonoglyceride in an amount of 5 to 99.9%, preferably 40 to 99.9%, morepreferably 60 to 99.5%, especially 75 to 99%. The fatty acidconstituents are preferably contained in amounts of 15 to 90% ofα-linolenic acid, 1 to 80% of oleic acid and 2 to 50% of linoleic acid.

[0015] The diglyceride to be used in the present invention is preferredto have fatty acid constituents similar to those of the monoglyceride.

[0016] In the oil/fat composition of the present invention, thediglyceride is present in an amount of 0.1 to 49.9%. It is addedpreferably in an amount of 0.1 to 25%, more preferably 0.5 to 10%,especially preferably 1 to 5% in order to have taste masking effects andto allow the monoglyceride to exhibit its maximum effect. Moreover, thediglyceride and monoglyceride are preferably incorporated at a weightratio less than 1, preferably 0.01 to 0.8.

[0017] The oil/fat composition of the present invention may contain atriglyceride and a free fatty acid.

[0018] The triglyceride is added, as a balancing component for theoil/fat composition, in an amount not greater than 94.9%, preferably notgreater than 59.9%, more preferably not greater than 39.5%, especiallypreferably not greater than 24% based on the oil composition, in orderto have taste masking effects and allow the monoglyceride to exhibit itsmaximum effect.

[0019] The triglyceride has, as a fatty acid constituent, 40% or less,preferably 25% or less, especially preferably 20% or less of an ω3-unsaturated fatty acid from the viewpoint of stability againstoxidation. It contains an unsaturated fatty acid in an amount of 55 to100%, preferably 70 to 100%, more preferably 80 to 100%, especiallypreferably 90 to 100%.

[0020] In the oil/fat composition of the present invention,polyunsaturated fatty acids, such as eicosapentaenoic acid,docosahexaenoic acid and arachidonic acid, having at least fourcarbon-to-carbon double bonds are required to be incorporated in anamount not greater than 20% of all the fatty acid constituents from theviewpoint of stability against oxidation. Their content is preferably10% or less, more preferably 5% or less, especially preferably 2% orless, but the composition substantially free of these polyunsaturatedfatty acids is most preferred.

[0021] The above-described monoglyceride is available by any one ofhydrolysis reaction of a linseed oil, perilla oil, soybean oil orrapeseed oil containing an ω 3-unsaturated acyl group or ω 6-unsaturatedacyl group, ester exchange reaction of the above-exemplified oil or fatwith glycerin, or esterification of a fatty acid derived from such anoil or fat with glycerin. The reaction method may be either one ofchemical reaction in the presence of an alkali catalyst or biochemicalreaction using an enzyme such as lipase. From the viewpoint ofindustrial productivity, chemical reaction using alkali catalyst is morepreferred

[0022] The oil/fat composition of the present invention is preferablyemployed after purification through degumming, acid removing, washingwith water, decoloring or deodorizing from the viewpoints of heatstability and taste. It is preferred that the composition contain a freefatty acid, or salt thereof, in an amount of 3.5% or less, preferably2.5% or less, more preferably 1.5% or less, especially preferably 1% orless, most preferably 0.5% or less. In addition, it should have aperoxide value (POV, Standard Method for Analysis of Oils, Fats andDerivatives 2.5.2.1 of Japan Oil Chemists' Society) of 10 or less,preferably 7 or less, more preferably 5 or less, especially 3 or less,most preferably 1 or less. Color, referred to in the specification ascolor (10R+Y), is measured by the Lovibond method (Standard Method forAnalysis of Oils, Fats and Derivatives 2.2.1.1 of Japan Oil Chemists'Society, 5 1/4 inch glass cell is used) is preferably 35 or less,referably 30 or less, especially 25 or less.

[0023] A preferred oil/fat composition of the present invention is onehaving a POV of 3 or less and a color (10R+Y) of 30 or less, andcomprises 60 to 99.5% of the monoglyceride, 0.5 to 10% of thediglyceride, 39.5% or less of the triglyceride and 1% or less of a freefatty acid, or salt thereof, wherein the monoglyceride has, as fattyacid constituents thereof, 30 to 70% of α-linolenic acid, 10 to 50% ofoleic acid, 5 to 40% of an ω 6-unsaturated fatty acid and 80 to 100% ofan unsaturated fatty acid, and a fatty acid having at least twocarbon-to-carbon double bonds/ω 9-unsaturated fatty acid+saturated fattyacid) at a weight ratio of 1.2 to 5; and the content of apolyunsaturated fatty acid having at least 4 carbon-to-carbon doublebonds is 2% or less in all the fatty acid constituents.

[0024] A more preferred oil/fat composition of the present inventionwill have a POV of 1 or less and color (10R+Y) of 25 or less, andcomprises 75 to 99% of the monoglyceride, 1 to 5% of the diglyceride,24% or less of the triglyceride and 0.5% or less of a free fatty acid,or salt thereof, wherein the monoglyceride have, as fatty acidconstituents thereof, 40 to 65% of α-linolenic acid, 12 to 30% of oleicacid, 10 to 30% of an ω 6-unsaturated fatty acid, 90 to 100% of anunsaturated fatty acid, and a fatty acid having at least twocarbon-to-carbon double bonds/(ω 9-unsaturated fatty acid+saturatedfatty acid) at a weight ratio of 1.5 to 4; and the content of apolyunsaturated fatty acid having at least 4 carbon-to-carbon doublebonds is 0% in all the fatty acid constituents.

[0025] The oil/fat composition of the present invention will preferablycontain a phytosterol in an amount of 0.05% or greater, especially 0.3%or greater from the point of view of cholesterol lowering effects. Thecontent of a phytosterol in the oil/fat composition will depend on itsraw material oil/fat or preparation process. For example, when acommercially available fatty acid obtained by distillation is used as araw material, the content of the phytosterol in the oil/fat compositionwill be lowered. In this case, it is preferred to add phytosterol toprovide a content of 0.05% or greater. Although no particular limitationis imposed on the upper limit of its content, a range of 0.05% to 1.2%is preferred. It may be added in an amount of 1.2% or greater whenfurther cholesterol reduction is intended. Examples of the phytosterolinclude compounds in free form such as α-sitosterol, β-sitosterol,stigmasterol, campesterol, α-sitostanol, β-sitostanol, stigmastanol,campestanol and cycloartenol; and compounds in ester form such as theirfatty acid esters, ferulate esters and cinnamate esters.

[0026] The oil/fat composition of the present invention may contain anantioxidant. No limitation is imposed on the antioxidant insofar as itsnormal use in foods or pharmaceuticals. Combination of one or more ofcatechin, tocopherol, vitamin C fatty acid esters, phospholipid andnatural antioxidant components is preferred, with tocopherol andcatechin are particularly preferred. Examples of the vitamin C fattyacid esters include palmitate esters and stearate esters, while those ofthe natural antioxidant components include herbs such as rosemary andextracts from the leaves or roots of a peach. The antioxidant ispreferably added to the oil/fat composition of the present invention inan amount of 0.01 to 5%, especially 0.05 to 1%.

[0027] It is preferred to add a crystallization inhibitor to the oil/fatcomposition of the present composition.

[0028] Examples of suitable crystallization inhibitors which may be usedinclude polyol fatty acid esters, such as polyglycerin-condensedricinoleate esters, polyglycerin fatty acid esters, sucrose fatty acidesters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acidesters, and propylene glycol fatty acid esters.

[0029] As the polyol fatty acid esters, those having an HLB (calculationformula of Griffin) of 4 or less, especially polyglycerin fatty acidesters, sucrose fatty acid esters and sorbitan fatty acid esters havingan HLB of 3 or less are preferred.

[0030] The crystallization inhibitor is preferably added to the oil/fatcomposition in an amount of 0.02 to 0.5%, especially 0.05 to 0.2%.

[0031] The oil/fat composition thus obtained has excellent physiologicalaction, such as improved hepatic function, improved body fat, visceralfat and blood triglyceride burning properties, and are seen to lower theblood sugar level, the blood pressure level, and improve insulinresistance, lowering PAI-I and lowering leptin. Moreover, it hasexcellent processing properties and taste. Since an ω 3-unsaturated acylgroup exists not as a free fatty acid but as an acyl group constitutingthe monoglyceride, the composition is active even at low concentrationsand has an immediate effect. It is also characterized by a pleasanttaste and is safe. These properties make it possible to use the oil/fatcomposition of the present invention for foods, feeds andpharmaceuticals.

[0032] The oil/fat composition of the present invention can be used inoil/fat-containing foods. Specific examples include capsules, tablets,granules, powders, bakery foods such as breads, cakes, cookies, pies,pizza crusts and bakery mixes, oil-in-water type oil/fat-containingfoods such as soups, dressings, mayonnaise, coffee whiteners, whip creamand ice cream, water-in-oil type oil/fat-containing foods such asmargarine, spread and butter creams, confections, for example,chocolate, caramels, candies, snacks such as potato chips, and dessert,beverages, sauces, barbecue sauces, peanut butter, baking shortening,dough, fillings, enrobers, meat processed foods, such as ham, sausageand hamburg steak, noodles, frozen foods, retort foods, cheeses androux. The above-exemplified oil/fat-containing food can be prepared byadding, in addition to the above-described oil/fat composition, avariety of ordinary food materials depending on the type of food. Theamount of the oil/fat composition of the present invention to be addedto the food varies depending on the kind of the food, but is usually 0.1to 100%, preferably 1 to 80%, especially 2 to 80%. It is preferablyadded in an amount of 0.1 to 50 g, preferably 0.5 to 10 g, especially 1to 7.5 g, interms of the oil/fat composition once or several times aday. When a food contains an oil/fat derived from its basic ingredients,the ratio of the oil/fat derived from the material to the oil/fatcomposition of the present invention will be preferably 95:5 to 1:99,more preferably 95:5 to 5:95, still more preferably 85:15 to 5:95,especially preferably 40:60 to 5:95.

[0033] As the above-exemplified foods, examples of oil/fat containingfood snacks include those containing 1 to 30%, preferably 1 to 20% of anoil/fat, 0 to 20%, preferably 1 to 20%, especially 2 to 15% of aphytosterol, 40 to 99% of a carbohydrate, and 0 to 20%, preferably 1 to10% of a carbonating agent. The oil/fat used here has the followingconstitution: POV is 10 or less, preferably 3 or less, especiallypreferably 1 or less; the content of a monoglyceride is 5 to 99.9%,preferably 60 to 99.50, especially preferably 75 to 99%; a weight ratioof the content of the monoglyceride to diglyceride is 1 or less; themonoglyceride has, as its fatty acid constituent, 20 to 80%, preferably30 to 70%, especially 40 to 60% of α-linolenic acid, 10 to 50%,preferably 12 to 30% of oleic acid and 5 to 40%, preferably 10 to 30% oflinoleic acid; and a content of a polyunsaturated fatty acid having atleast 4 carbon-to-carbon double bonds, in all the fatty acidconstituents in the oil/fat, is 20% or less. Examples of thecarbohydrate usable here include sucrose, glucose, fructose, maltose,xylitol, sorbitol, erythritol and starch, those of the carbonating agentinclude those composed of an effervescing agent such as sodiumbicarbonate and acidic agent such as tartaric acid, fumaric acid orcitric acid. By using such food materials, oil/fat-containing a foodsnack such as a tablet, candy, caramel and gummy candy can be preparedin a conventional manner. The addition of a carbonating agent makes thefood especially appetizing.

[0034] Examples of pharmaceutical uses include orally administrableagents, e.g., solid preparations such as powders, granules, capsules,pills and tablets, liquid preparations such as aqueous preparations,suspensions and emulsions, and gel preparations. These types of orallyadministrable agents can be prepared by adding, in addition to theoil/fat composition, excipient, disintegrator, binder, lubricant,surfactant, alcohol, water, water-soluble polymer, sweetening agent,taste corrigent and acidifier, each ordinarily employed according to thedosage form of the orally administrable agent. Examples of the orallyadministrable preparation include cerebral function improvers. Theamount of the oil/fat composition of the present invention to be addedto an orally-administrable preparation differs with its using purpose ordosage form, but it is usually added in an amount of 0.1 to 100%,preferably 1 to 80%, especially 5 to 8.0. As a dose, 0.1 to 50 g,preferably 0.5 to 10 g, especially 1 to 7.5 g, in terms of the oil/fatcomposition, is preferably administered once or several times a day.

[0035] Examples of feed uses include livestock feed for cows, pigs, fowland sheep, feed for small animals such as rabbits, rats and mice, feedfor fishes such as eel, porgy, yellowtail and shrimp and pet foods fordogs, cats, birds and squirrels. Although the amount of the oil/fatcomposition of the present invention to be added to feed differsdepending on the using purpose of the feed, it is usually added in anamount of 1 to 30%, with 1 to 20% being especially preferred.

[0036] The oil/fat of the present invention is preferably administeredas a component of a food composition to a patient in need of reducingglutamic oxaloacetic transaminase, reducing glutaminic pyruvictransaminase, reducing body weight, reducing visceral fat weight, ortreating obesity, said administration preferably being oral.

EXAMPLES Example 1

[0037] The following oil/fat composition was prepared.

[0038] Oil/fat Composition 1

[0039] A mixture of 300 parts by weight of perilla oil (product of OhtaOil Mill Co., Ltd.), 120 parts by weight of glycerin and 0.04 part byweight of calcium hydroxide was reacted at 220° C. for 1 hour in anitrogen gas atmosphere, followed by neutralization with phosphoricacid. The resulting product was degassed at 200° C. and 1.3hPa by usinga thin-film evaporator. An initial distillate at 180° C. and 0.4 hPa wascut and a distillate at 200° C. and 0.07 hPa was collected. Glycerin wasthen removed at 175° C. and 0.1 hPa (redistilling), whereby Oil/fatcomposition 1 was obtained.

[0040] Oil/Fat Composition 2

[0041] Oil/fat composition 2 was obtained by mixing 70 parts by weightof oil/fat composition 1 and 30 parts by weight of rapeseed oil (productof The Nisshin Oil Mills Ltd.).

[0042] Oil/Fat Composition 3

[0043] Oil/fat composition 3 was obtained by mixing 200 parts by weightof linseed oil (product of Yoshihara Oil Mill, Ltd.), 100 parts byweight of olive oil (Wako Pure Chemical Industries, Ltd.), 120 parts byweight of glycerin and 0.04 part by weight of calcium hydroxide andreacting and treating the resulting mixture in a similar manner tooil/fat composition 1.

[0044] Oil/Fat Composition 4

[0045] To a mixture of 650 parts by weight of rapeseed fatty acid and107 parts by weight of glycerin was added “Lipozyme IM” (Novo NordiskBioindustry Co., Ltd.) and esterification reaction was conducted at 40°C. and 0.07 hPa for 5 hours. The reaction mixture was subjected tomolecular distillation (235° C., 0.07 hPa). The residue was collected.After washing with water, deodorization was conducted at 235° C. for 1hour, whereby Oil/fat composition 4 was obtained.

[0046] Oil/Fat Composition 5

[0047] Under similar conditions to those employed for Oil/fatcomposition 4, 325 parts by weight of oleic acid (product ofSigma-Aldrich) and 107 parts by weight of glycerin were esterified for 3hours. The reaction mixture was subjected to molecular distillation(200° C., 0.07 hPa) and the resulting distillate was collected. Thedistillate was fractionated by chromatography on a silica gel columnwhile using hexane: ethyl acetate as an eluting solvent (first, 100:0,then 90:10, then 80:20 and finally 70:30). The final eluent wascollected, and the solvent was then removed by evaporation, wherebyOil/fat composition 5 was obtained.

[0048] Oil/Fat Composition 6

[0049] In a similar manner to that employed for Oil/Fat Composition 5except for the use of -linolenic acid (product of Tokyo Kasei Kogyo Co.,Ltd.) instead of oleic acid, reaction and treatment were conducted,whereby Oil/fat composition 6 was obtained.

[0050] Oil/Fat Composition 7

[0051] After 300 parts by weight of “DHA 45” (product of MaruhaCorporation), 120 parts by weight of glycerin and 0.9 part by weight ofsodium methoxide were mixed and reacted at 100° C. for 4.5 hours under anitrogen gas atmosphere, the reaction mixture was neutralized withphosphoric acid. The resulting product was subjected to moleculardistillation (200° C., 0.07 hPa) and a distillate was collected. Thedistillate was then fractionated by chromatography on a silica gelcolumn while using hexane and ethyl acetate as an eluting solvent (theirratio was similar to that employed in the preparation of Oil/fatcomposition 5). After each fraction was evaporated and the solvent wasremoved, each residue was mixed again, whereby Oil/fat composition 7 wasobtained.

[0052] In Table 1, the oil/fat compositions thus prepared and analyticalresults of fatty acids constituting a monoglyceride are shown. TABLE 1Oil/fat composition Invention product Comparative product 1 2 3 4 5 6 7Glycerides TG 0.0 29.4 3.8 13.5 0.0 0.0 0.0 composition *1 DG 4.1 3.232.0 85.1 0.0 0.0 3.7 MG 95.9 67.3 64.2 1.1 100.0 100.0 96.3 FFA 0.0 0.10.0 0.3 0.0 0.0 0.0 AV ≦0.1 ≦0.22 ≦0.1 ≦0.62 ≦0.1 ≦0.1 ≦0.1 POV 0.3 0.240.38 0.19 0.1 0.1 1.06 Color (10 R + Y) 24.5 21.8 26.6 13.7 8.7 12.133.5 MG-constituting C18:3 3 58.9 58.8 40.5 10.5 0.0 78.2 0.0 fattyacids *2 C20:5 0.0 0.0 0.0 0.0 0.0 0.0 6.7 C22:6 0.0 0.0 0.0 0.0 0.0 0.046.3 C16:1 0.0 0.0 0.2 0.0 0.0 0.0 0.0 C18:1 9 12.8 13.1 34.3 57.0 99.10.7 10.5 C20:1 0.0 0.0 0.0 1.7 0.0 0.0 1.4 C22:1 0.0 0.0 0.0 1.0 0.0 0.01.1 C18:2 6 16.4 16.5 14.0 21.9 0.0 19.5 1.3 C16:0 5.6 5.6 7.7 3.7 0.00.0 11.3 C18:0 1.5 1.5 3.0 1.8 0.0 0.0 2.7 A ratio having at least 3.83.7 1.2 0.5 0.0 139.6 2.0 two double bonds *3

Example 2

[0053] C57BL/6J male mice aged 7 weeks (a model of dietary type IIdiabetes) were divided into 6 groups, each group consisting of 5 miceand fed with the below-described diet for 4 weeks. After the rats werefasted for 18 hours, the blood was collected from the aorta abdominalisunder anesthesia with ether. GOT activity and GPT activity of the serumseparated from the blood were measured using asparaginic acid andalanine as substrates, respectively, in accordance with the Karmenmethod (J. Clin. Invest. 34, 131, 1955). The values relative to those ofthe control diet set at 100 are shown in Table 2. Diet composition:Control diet Test diet Casein 20.0% 20.0% Soybean oil 20.0 20.0 Lard10.0 10.0 Oil/fat composition 0.0 4.0 Mineral mixture 3.5 3.5 Vitaminmixture 1.0 1.0 Cellulose 4.0 4.0 Sucrose 13.0 13.0 Starch 28.5 24.5

[0054] TABLE 2 GOT GPT Weight Visceral fat Oil/fat composition activityactivity gain weight Invention 1 81.6* 55.4* 67.3* 56.2* Products 285.1* 77.3* — — 3 86.9 79.2* — — Comparative (Control diet) 100 100 100100 Products Perilla oil 121 113 122* 117* 5 110 108 — —

[0055] Visceral fat weight; total of perinephric, mesenteric,retroperitoneal and epididymal fat weights.

[0056] The oil/fat compositions according to the present invention eachexhibited excellent effects for lowering GOT and GPT levels in blood andreducing a body weight and a visceral fat weight.

Example 3

[0057] The results of hydration property and standing stability of theoil/fat composition are shown in Table 3.

[0058] Test on hydration property: By a disperser, 1 part by weight ofan oil/fat composition and 99 parts by weight of water were stirred (for5 minutes at 10000 r/min). The reaction mixture was allowed to stand at5° C. for 24 hours and the condition was visually observed based on thefollowing standards.

[0059] Evaluation Surface condition

[0060] A: No floating of an oil is observed on the surface.

[0061] B: Slight floating of an oil is observed on a part of thesurface.

[0062] C: Floating of an oil is observed

[0063] D: The mixture is turbid and existence of an oil layer isrecognized.

[0064] Test on static stability: An oil/fat composition was allowed tostand at 35° C. for 24 hours and the condition of the composition wasvisually observed based on the following standards:

[0065] Evaluation Condition

[0066] A: The composition is transparent.

[0067] B: A slight turbidity is recognized.

[0068] C: The composition is turbid but has fluidity.

[0069] D: The composition is turbid and lacks fluidity. Oil/fatcomposition Hydration property Static stability Invention product 1 A A2 B A 3 B A Comparative product 4 C A 7 A D Perilla oil C A

[0070] The invention products were transparent when allowed to stand at35° C. so that it has good workability, melts well in the mouth, hasgood hydration property and has excellent processing properties.

Example 4

[0071] Tablets were prepared as follows. An oil/fat composition wasprepared by mixing 100 parts by weight of Oil/fat composition 1, 0.02part by weight of Mix Vitamin E “MDE-6000” (product of Yashiro Co.,Ltd.), 0.5 part by weight of catechin “Sunkatol No. 1” (product of TaiyoKagaku Co., Ltd.), 0.25 part by weight of rosemary “Herbalox type HT-0Extract” (product of Kalsec, Inc.) and 2.0 parts by weight of aphytosterol (product of Tama Biochemical Co., Ltd.). A mixture of 10parts by weight of the resulting oil composition, 44 parts by weight ofcorn starch, 40 parts by weight of crystalline cellulose, 5 parts byweight of carboxymethylcellulose calcium, 0.5 part by weight of silicicanhydride and 0.5 part by weight of magnesium stearate was compressedinto tablets (each, 200 mg in weight).

Example 5

[0072] Soft capsules were prepared as follows. An oil/fat compositionwas prepared by mixing 100 parts by weight of Oil/fat composition 1,0.02 part by weight of “Mix Vitamin E MDE-6000” (product of Yashiro Co.,Ltd.), 0.7 part by weight of catechin “Sunkatol No.1” (Taiyo Kagaku Co.,Ltd.), 0.02 part by weight of Vitamin C palmitate (product of Roche,Ltd.), 0.1 part by weight of a phytosterol (product of Tama BiochemicalCo., Ltd.) and 0.15 part by weight of polyglycerin fatty acid ester“THL3” (product of Sakamoto Yakuhin Kogyo Co., Ltd.). The resultingoil/fat composition (300 mg) was encapsulated in oval-shaped softcapsules, whereby soft capsules were prepared.

Example 6

[0073] Hamburg steaks were prepared as follows. The below-described foodmaterials were mixed under stirring in a food processor and formed intooblong patties, each 80 g. After baking them on a hot plate at 230° C.for 2 minutes, they were heated in an oven at 200° C. for 7 minutes.They were wrapped individually and quick frozen at −40° C. for 40minutes. After they were preserved at −20° C. for 1 week, they wereboiled for 10 minutes and provided for tasting. Composition ratio offood materials: Minced meat (beef:pork = 7:3) 65.0% Onion (roasted) 10.0Whole egg 5.0 Soybean protein 5.0 Crumbled bread 5.0 Corn starch 2.0Salt 1.0 Nutmeg 0.3 Pepper 0.2 Water 6.5 Oil/fat composition* (Table 4)1.5

[0074] Average evaluation by a panel of 10 experts based on thefollowing standards is shown in Table 4. Evaluation Taste Juicy feelSoft feel A Very delicious Very juicy Very soft B Delicious Juicy Soft CNot so delicious Slightly dry Slightly hard D Distasteful Dry Hard

[0075] TABLE 4 Oil/fat composition 2 6 7 Perilla Oil Taste A C D B Juicyfeel A A A C Soft feel A A A C

[0076] It has been found that hamburg steaks made using Oil/fatcomposition 2 of the present invention were soft, juicy, rich in taste,not greasy and were utterly free from a rancid odor due todeterioration, had excellent processing properties, and were markedlydelicious.

Example 7

[0077] The boiled noodles were prepared as follows. For 15 minutes, 100parts by weight of wheat flour, 32 parts by weight of water, 2 parts byweight of salt and 0.5 part by weight of an oil/fat composition werekneaded. The kneaded mass was then allowed to stand for 30 minutes atroom temperature, spread under pressure and cut into noodles. Afterboiling for 15 minutes in boiling water of 10 times the weight of thenoodles, they were cooled with running water and drained, whereby boilednoodles were obtained. These noodles refrigerated at 10° C. for one daywere boiled for 1 minute and provided for tasting.

[0078] Average evaluation of a panel of 10 experts based on thefollowing evaluation standards is shown in Table 5. Evalu- Separabilityof ation Taste Surface luster noodles A Very delicious Very lustrousVery good B Delicious Lustrous Good C Not so delicious Not so lustrousNot so good D Bad taste Having no luster Bad

[0079] TABLE 5 Oil/fat composition Perilla 1 7 oil Taste A C B Surfaceluster A A D Separability of noodles A A D

[0080] It has been found that boiled noodles made using Oil/fatcomposition 1 of the present invention had a smooth surface, had luster,did not stick to each other and were separated easily, were rich intaste, were not greasy and were utterly free from a rancid odor due todeterioration, had excellent processing properties, and were markedlydelicious.

Example 8

[0081] The tablets of candy having the following composition wereprepared. Parts by weight Xylitol 28.4 Sorbitol 56.9 Oil/fat composition1 2.5 Phytosterol 2.5 (product of Tama Biochemical Co., Ltd.) Flavor(ginger oil) 1.2 Citric acid 3.0 Sodium bicarbonate 5.0 Colorant(turmeric powder) 0.5

[0082] After the above-described raw materials were mixed, the mixturewas ground in a mortar. The resulting grind was compressed (24.5 Mpa, 4seconds) into tablets of candy, each 2 g in weight, in a conventionalmanner by a tableting machine.

INDUSTRIAL APPLICABILITY

[0083] The oil/fat composition according to the present invention hasexcellent processing properties, pleasant taste and excellent activitycapable of lowering glutamic oxaloacetic transaminase (GOT) and glutanicpyruvic transaminase (GPT) levels in the blood. It is useful not onlyfor pharmaceuticals but also for preventive or remedial foods or feedseffective for hepatic function disturbances or obesity.

[0084] This application is based on Japanese application, 2000-239574,filed in the Japanese Patent office on Aug. 8, 2000, the entire contentsof which are hereby incorporated by reference.

1. An oil/fat composition comprising 5 to 99.9 wt. % of a monoglyceride having, as a fatty acid constituent thereof, 15 to 90 wt. % of an ω 3-unsaturated fatty acid having less than 20 carbon atoms, 1 to 80 wt. % of an ω 9-unsaturated fatty acid and 2 to 50 wt. % of an ω 6-unsaturated fatty acid; and 0.1 to 49.9% of a diglyceride, wherein the weight ratio of the diglyceride to the monoglyceride is less than 1 and the content of polyunsaturated fatty acid having at least 4 carbon-to-carbon double bonds is 20 wt. % or less of all the fatty acid constituents.
 2. An oil/fat composition according to claim 1, which has a POV of 10 or less and contains α-linolenic acid as the ω 3-unsaturated fatty acid.
 3. An oil/fat composition according to claim 1 or 2, which has a POV of 3 or less, has a color (10R+Y) of 30 or less, comprises 60 to 99.5 wt. % of the monoglyceride, 0.5 to 10 wt. % of the diglyceride, 39.5 wt. % or less of a triglyceride and a free fatty acid, or salt thereof, of 1 wt. % or less, wherein the monoglyceride has, as a fatty acid constituent thereof, 30 to 70 wt. % of α-linolenic acid, 10 to 50 wt. % of oleic acid, 5 to 40 wt. % of the ω 6-unsaturated fatty acid, 80 to 100 wt. % of an unsaturated fatty acid, and a fatty acid having at least two carbon-to-carbon double bonds/(α9-unsaturated fatty acid+saturated fatty acid) at a weight ratio of 1.2 to 5; and the content of fatty acids having at least 4 carbon-to-carbon double bonds is 2 wt. % or less.
 4. An oil/fat composition according to claim 1 or 2, which has a POV of 1 or less, has a color (10R+Y) of 25 or less, comprises 75 to 99 wt. % of the monoglyceride, 1 to 5 wt. % of the diglyceride, 24 wt. % or less of a triglyceride and a free fatty acid, or salt thereof, of 0.5 wt. % or less, wherein the monoglyceride has, as a fatty acid constituent thereof, 40 to 65 wt. % of α-linolenic acid, 12 to 30 wt. % of oleic acid, 10 to 30 wt. % of the ω 6-unsaturated fatty acid, 90 to 100 wt. % of an unsaturated fatty acid; and the content of a fatty acid having at least two carbon-to-carbon double bonds/(ω 9-unsaturated fatty acid+saturated fatty acid) at a weight ratio of 1.5 to 4; and the content of a fatty acid having at least 4 carbon-to-carbon double bonds is 2 wt. % in all the fatty acid constituents.
 5. An oil/fat composition according to any one of claims 1 to 4, further comprising a phytosterol in an amount of 0.05 wt. % or more.
 6. An oil/fat composition according to any one of claims 1 to 4, further comprising 0.02 to 0.5 wt. % of a crystallization inhibitor.
 7. An oil/fat composition according to any one of any one of claims 1 to 4, further comprising 0.01 to 5 wt. % of an antioxidant.
 8. A food containing an oil/fat composition as claimed in any one of claims 1 to
 7. 9. A feed containing an oil/fat composition as claimed in any one of claims 1 to
 7. 10. A pharmaceutical composition containing an oil/fat composition as claimed in any one of claims 1 to
 7. 11. Method of preparing a food article comprising mixing one or more food materials with the oil/fat composition of as claimed in any one of claims 1 to
 7. 12. A method of reducing glutamic oxaloacetic transaminase and glutamic pyruvic transaminase in the blood comprising administering to a patient in need thereof, a food composition comprising the oil/fat composition as claimed in any one of claims 1 to
 7. 13. The method as claimed in claim 16, wherein said food composition comprises said oil/fat composition in an amount of 0.1 to 100%.
 14. A method of reducing body weight and visceral fat weight in an human or an animal comprising administering to a patient in need thereof, a food composition comprising the oil/fat composition as claimed in any one of claims 1 to
 7. 15. The method as claimed in claim 18, wherein said food composition comprises said oil/fat composition in an amount of 1 to 80%.
 16. A method of treating obesity comprising administering to a patient in need thereof, a food composition comprising the oil/fat composition as claimed in any one of claims 1 to
 7. 17. The method as claimed in claim 20 wherein said food composition comprises said oil/fat composition in an amount of 2 to 80%. 